Sodium Carbonate → 3-(3,5-difluorophenyl)benzoic Acid

HRID 1740285Notes

Reaction equation

HRID 1740285 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([F:8])[CH:7]=1.I[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([OH:18])=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=[O:17])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 120603-Iodobenzoic acidHCID 2734338(3,5-Difluorophenyl)boronic acid

Product 1

HCID 114248163-(3,5-difluorophenyl)benzoic Acid

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

The mixture of 3,5-difluorophenyl-dihydroxyborane (3 g), 3-iodobenzoic acid (3.37 g), sodium carbonate (4.31 g) and palladium(II) acetate (0.030 g) in water (60 ml) was stirred at room temperature for six hours. The reaction mixture was filtered and was washed with ether (30 ml) twice. The aqueous layer was adjusted to pH 2 with 6N hydrochloric acid. The crystalline was collected, washed with water and dried to afford 3-(3,5-difluorophenyl)benzoic acid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwas washed with ether (30 ml) twice
  3. customThe crystalline was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-f0d7d2a8d1024ef284cac325d0f30f09
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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